Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-09-05
2004-03-23
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S341500
Reexamination Certificate
active
06710181
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel imidazole/monocarboxylic acid derivative, and also to a surface treatment agent that has this imidazole/monocarboxylic acid derivative as an active ingredient and is for improving the adhesion between a metal such as copper, steel or aluminum or an inorganic material such as glass fiber, silica, aluminum oxide or aluminum hydroxide and a resin, a resin additive that has this imidazole/monocarboxylic acid derivative as an active ingredient and is for improving the adhesive strength and mechanical strength of a resin such as an epoxy resin, and a resin composition—in particular a polyimide resin composition—that contains this imidazole/monocarboxylic acid derivative.
BACKGROUND ART
A board of an electronic device is made by heating copper foil and a phenol-resin-impregnated paper substrate, an epoxy-resin-impregnated glass substrate or the like while pressurizing to produce a copper-clad laminate, and then forming an electric network by etching, and mounting elements such as semiconductor devices on top.
During the manufacturing process, the copper foil is bonded to the substrate, and they are heated, immersed in acidic or alkaline solutions, a resist ink applied thereto, soldered, and hence the copper foil and the substrate are required to have various properties. To satisfy these requirements, with regard to the copper foil, studies have been carried out subjecting the copper foil to brass layer formation treatment (Japanese Patent Publication Nos. S51-35711 and S54-6701), chromate treatment, zinc-chromium mixture coating treatment in which the coating includes zinc or zinc oxide and chromium oxide (Japanese Patent Publication No. S58-7077), treatment with a silane coupling agent, and the like. Moreover, with regard to the resin, the requirements are satisfied by changing the type of resin and/or curing agent and/or the mixing proportions thereof, by adding additives, and so on. Moreover, in the case of glass fiber, surface treatments using a silane coupling agent or the like have been studied. However, in recent years, there have been advances in miniaturization of printed circuits, and the properties required of the boards used in electronic devices have become ever more stringent.
To cope with the required improvement in etching precision that goes along with the above, the Matte side of the copper foil bonded to the prepreg is required to have a lower surface roughness (i.e. a low profile). However, the surface roughness of the Matte side produces an anchoring effect so as to bond the prepreg tightly, and hence the requirement of a low profile goes against improving the adhesive strength, meaning that the reduction in the anchor effect upon lowering the profile must be compensated for by improving the adhesive strength by another means.
Moreover, a composite material in which an inorganic material such as silica or alumina is filled into an epoxy resin matrix is used as an electrically insulating casting material used, for example, in high voltage/high capacity devices and in sealing semiconductors in power plants. Various electrical and mechanical properties are required of such a material, and to satisfy these requirements it is necessary to improve the adhesion between the inorganic material and the resin. Measures such as adding a silane coupling agent into the resin or subjecting the inorganic material to surface treatment with a silane coupling agent have been proposed, but further improvement of the resin/inorganic material interface is required.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a novel imidazole/organic monocarboxylic acid salt derivative reaction product that is capable of meeting these requirements, that is, that improves the adhesion between a metal such as copper, steel or aluminum or an inorganic material such as glass fiber, silica, aluminum oxide or aluminum hydroxide and a resin. Further, another object of the present invention is to provide a method for producing this imidazole/organic monocarboxylic acid salt derivative reaction product, and a surface treatment agent, resin additive and resin composition that use this imidazole/organic monocarboxylic acid salt derivative reaction product.
The inventors of the present invention carried out assiduous studies, and as a result discovered: if a metal or an inorganic material is subjected to surface treatment with an imidazole/organic monocarboxylic acid salt derivative reaction product obtained by reacting a specific imidazole compound with a silane compound having a glycidoxy group and then reacting with an organic monocarboxylic acid, then the adhesion of the metal or the inorganic material to a resin is improved; and furthermore, if such an imidazole/organic monocarboxylic acid salt derivative reaction product is added to a resin such as an epoxy resin, then the curing reaction of the resin is promoted and moreover the adhesive strength and the mechanical strength of the resin are improved.
The present invention was achieved based on the above findings, and is summarized as follows:
(1) An imidazole/organic monocarboxylic acid salt derivative reaction product obtained by reacting an imidazole compound represented by undermentioned general formula (1) with a silane compound having a glycidoxy group represented by undermentioned general formula (2) at 80 to 200° C., and then reacting with an organic monocarboxylic acid at 50 to 200° C.;
where, in general formulae (1) and (2), R
1
, R
2
and R
3
are each independently a hydrogen atom, a vinyl group, or an alkyl group having 1 to 20 carbon atoms, while R
2
and R
3
may together form an aromatic ring; R
4
and R
5
are each independently an alkyl group having 1 to 5 carbon atoms; m is an integer between 1 and 10; and n is an integer between 1 and 3.
(2) A method for producing the imidazole/organic monocarboxylic acid salt derivative reaction product as described in (1) above, comprising: reacting an imidazole compound represented by undermentioned general formula (1) with a silane compound having a glycidoxy group represented by undermentioned general formula (2) at 80 to 200° C.; and subsequently reacting with an organic monocarboxylic acid at 50 to 200° C.;
where, in general formulae (1) and (2), R
1
, R
2
, R
3
, R
4
, R
5
, m and n are as defined in (1) above.
(3) A surface treatment agent having the imidazole/organic monocarboxylic acid salt derivative reaction product as described in (1) above as an active ingredient.
(4) A resin additive having the imidazole/organic monocarboxylic acid salt derivative reaction product as described in (1) above as an active ingredient.
(5) A resin composition containing the imidazole/organic monocarboxylic acid salt derivative reaction product as described in (1) above.
(6) A polyimide resin composition containing the imidazole/organic monocarboxylic acid salt derivative reaction product as described in (1) above.
Following is a more detailed description of the present invention.
In above-mentioned general formulae (1) and (2), if any of R
1
, R
2
or R
3
is an alkyl group, then this alkyl group has 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms. Moreover, if R
2
and R
3
together form an aromatic ring, then this aromatic ring is preferably a benzene ring.
The imidazole/organic monocarboxylic acid salt derivative reaction product of the present invention can be manufactured by reacting an imidazole compound represented by undermentioned general formula (1) with a silane compound having a glycidoxy group represented by undermentioned general formula (2) at 80 to 200° C., and then reacting with an organic monocarboxylic acid at 50 to 200° C. The reaction mechanism is complicated, with networking through siloxane bonds occurring in part, but the main reactions can be represented by the following formulae.
In the above general formula, A indicates the organic monocarboxylic acid.
Preferable examples of the imidazole compound represented by above-mentioned general formula (1) include imidazole, 2-alkylimidazoles,
Kumagai Masashi
Tsuchida Katsuyuki
Flynn ,Thiel, Boutell & Tanis, P.C.
Nikko Materials Co., Ltd.
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